Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound

A synthetic method, imidazolo technology, applied in the field of organic synthetic chemistry, can solve the problems of numerous precursor steps, low yield, harsh reaction conditions, etc., and achieve the effect of short reaction time, simple operation, high efficiency and high yield synthesis

Inactive Publication Date: 2015-06-03
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Targetedly solve the problems of low Vilsmeier–Haack formylation yield (20–30%), harsh reaction conditions, and many steps in the precursor of intramolecular dehydrocyclization reaction

Method used

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  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound
  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound
  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3a preparation of

[0018]

[0019] Add to a 25 mL round bottom flask with a magnetic stirrer N, N - Dimethylformamide (DMF) (2 mL), cinnamaldehyde 1a (0.5 mmol), 2-aminopyridine (0.75 mmol), cuprous iodide (0.15 mmol) and acetic acid (1.0 mmol), after stirring evenly, put it into a 120°C oil bath and continue stirring. TLC detection substrate 1a After disappearing, add 1ml of water, continue heating for 0.5 hour, and the reaction ends. The reaction solution was poured into water (15 mL), extracted with dichloromethane (3×15 mL), and the organic phases were combined. Backwash 3 times with 60 ml of water. The organic phase was dried with anhydrous magnesium sulfate, suction filtered, and then the organic solvent was distilled off under reduced pressure, and finally subjected to silica gel column chromatography to obtain a white solid 3a , confirmed to be imidazo[1,2-a]pyridine-3-carbaldehyde compound ...

Embodiment 2

[0022] Embodiment 2 imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3b preparation of

[0023] The 2-aminopyridine in "Example 1" was replaced by p-methoxycinnamaldehyde, the reaction steps were the same as in "Example 1", the reaction temperature was 110°C, and the reaction time was 4 hours.

[0024] The experimental results are shown in Table 1.

[0025]

[0026] Spectral analysis data 3b :

[0027] 1 H NMR (500 MHz, CDCl 3 ) δ 10.05 (s, 1H), 9.65 (d, J = 6.5 Hz, 1H), 7.80-7.77 (m, 3H), 7.59-7.55 (m, 1H), 7.11 (td, J = 7.0 Hz, J = 1.0 Hz, 1H), 7.07-7.05 (m, 2H), 3.89 (s, 3H); 13 C NMR (CDCl 3 , 125 Hz) δ 179.4, 160.9, 158.1, 147.6, 131.0, 130.3, 128.7, 124.6, 120.3, 117.1, 115.0, 114.2, 55.3; HRMS (ESI) m / z calculated for C 15 h 13 N 2 o 2 [M+H] + : 253.0972, found 253.0974.

Embodiment 3

[0028] Example 3 imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3c preparation of

[0029] The 2-aminopyridine in "Example 1" was replaced with o-nitrocinnamaldehyde, the reaction steps were the same as in "Example 1", the reaction temperature was 140° C., and the reaction time was 5 hours. The experimental results are shown in Table 1.

[0030]

[0031] Spectral analysis data 3c :

[0032] 1 H NMR (500 MHz, CDCl 3 ) δ 9.81 (s, 1H), 9.61 (d, J = 7.0 Hz, 1H), 9.11 (d, J = 8.0 Hz, 1H), 7.80-7.74 (m, 2H), 7.70-7.60 (m, 3H), 7.20 (t, J = 7.0 Hz, 1H); 13 C NMR (CDCl 3 , 125 Hz) δ 177.9, 154.2, 149.6, 147.6, 133.0, 132.6, 130.7, 130.5, 128.6, 127.2, 124.9, 121.2, 117.7, 115.8; HRMS (ESI) m / z calculated for C 14 h 10 N 3 o 3 [M+H] + : 268.0717, found 268.0718.

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Abstract

The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a simple and easy one-step method for synthesizing imidazo[1,2-a]pyridine-3-carbaldehyde compounds. Provided is a method for synthesizing imidazo[1,2-a]pyridine-3-carbaldehyde compounds in one step through [3+2] cyclization reaction of 2-aminopyridine and cinnamaldehyde. The method has simple and easy-to-obtain raw materials and steps Simple and efficient—avoid multi-step synthesis of reaction precursors, effectively shorten reaction time, and expand the application range of products, etc. Especially with 2-aminopyrimidine / pyrazine, imidazo[1,2-a]pyrimidine / pyrazine derivatives can be synthesized in one step. It is suitable for the synthesis of various imidazo[1,2-a]pyridine compounds. By this method, drug molecules Alpidem and Zolipidem can be synthesized with high efficiency and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, in particular to a simple and easy one-step synthesis of imidazo[1,2- a ] The method of pyridine-3-carboxaldehyde compounds. Background technique [0002] Imidazopyridine compounds are a very important class of nitrogen-containing fused heterocyclic compounds, which are widely used in synthesis, medicine, pesticide and dye industries. Common imidazopyridine compounds—imidazo[1, 2-a]pyridine derivatives are not only numerous in number, but also complex in structure. Derivatives based on imidazo[1,2-a]pyridine have attracted much attention due to their superior anti-tumor, anti-virus, sedative-hypnotic, anti-inflammatory and other biological activities, and many of them have become marketed drugs, such as Vasodilators Olprinone, sleeping pills Alpidem, Zolipidem, etc. The design and synthesis of imidazo[1, 2-a]pyridine derivatives and the research on the synthesis methodolo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D487/04
Inventor 毕锡和方桂春张林廖沛球
Owner NORTHEAST NORMAL UNIVERSITY
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